835-11-0

Usage

Preparation

Preparation by diazotization of 4,4′-diamino-2,2′- di-hydroxybenzophenone in diluted hydrochloric acid, followed by treatment with 50% phosphorous acid at 0° for 1 h, then at r.t. for 24 h (34%).

Upstream product

• 90-47-1 xanth-9-one 
• 134-55-4 phenyl 2-acetoxybenzoate 
• 7446-70-0 aluminium trichloride 
• 98-95-3 nitrobenzene 
• 609-65-4 o-chlorobenzoyl chloride 
• 2467-02-9 Bis(2-hydroxyphenyl)methane 
• 533-58-4 2-Iodophenol 
• 90-02-8 salicylaldehyde 
• 673-22-3 2-Hydroxy-4-methoxybenzaldehyde 
• 135-02-4 ortho-anisaldehyde 
• 77464-21-2 2-methoxy-α-(2-methoxyphenyl)benzenemethanol 
• 578-57-4 2-bromoanisole 
• 13102-33-5 2,2'-dimethoxybenzophenone 
• 201230-82-2 carbon monoxide 

Downstream Products

• 2467-02-9 Bis(2-hydroxyphenyl)methane 
• 17087-18-2 DL-N--β-phenyl-alanin 
• 17087-14-8 DL-N--leucin 
• 57443-93-3 (Z)-2-Amino-3-{[bis-(2-hydroxy-phenyl)-methylene]-amino}-but-2-enedinitrile 
• 91955-15-6 2,2'-Dihydroxy-benzophenon-hydrazon 
• 95950-25-7 2,2',2'',2'''-Tetrahydroxy-benzophenon-azin 
• 74697-53-3 2,2'-bis(benzyloxy)benzophenone 
• 97990-55-1 2,2'-Dihydroxybenzophenon-dimethylhydrazon 
• 117139-08-9 3-Chloro-4-(2-hydroxy-phenyl)-chromen-2-one 
• 21147-18-2 (2-hydroxyphenyl)(2-methoxyphenyl)methanone 
• 59410-99-0 (2-Hydroxy-phenyl)-(2-methoxymethoxy-phenyl)-methanone 
• 90-47-1 xanth-9-one 
• 7732-18-5 water 
• 124-38-9 carbon dioxide 

Relevant academic research and scientific papers

Selective Oxidation of Alkylarenes to the Aromatic Ketones or Benzaldehydes with Water

Here a palladium-catalyzed oxidation method for converting alkylarenes into the aromatic ketones or benzaldehydes with water as the only oxygen donor is reported. This C-H bond oxidation functionalization does not require other oxidants and hydrogen accep

C?H Oxygenation Reactions Enabled by Dual Catalysis with Electrogenerated Hypervalent Iodine Species and Ruthenium Complexes

The catalytic generation of hypervalent iodine(III) reagents by anodic electrooxidation was orchestrated towards an unprecedented electrocatalytic C?H oxygenation of weakly coordinating aromatic amides and ketones. Thus, catalytic quantities of iodoarenes in concert with catalytic amounts of ruthenium(II) complexes set the stage for versatile C?H activations with ample scope and high functional group tolerance. Detailed mechanistic studies by experiment and computation substantiate the role of the iodoarene as the electrochemically relevant species towards C?H oxygenations with electricity as a sustainable oxidant and molecular hydrogen as the sole by-product. para-Selective C?H oxygenations likewise proved viable in the absence of directing groups.

Rhodium-Catalyzed Directing-Group-Assisted Aldehydic C–H Arylations with Aryl Halides

A rhodium-catalyzed general protocol for the directing-group-assisted arylation of aromatic aldehydic C–H bonds was developed. This method involves either hydroxy- or amino-group-directed aldehyde C–H arylation with various aryl halides. A broad synthetic scope for the preparation of 2-hydroxybenzophenones was established with electronically variant salicylaldehydes and aryl halides with chemo- and regioselective possibilities. The developed protocol was also applied in the synthesis of medicinally important 3-salicyloylpyridines in high yields.

Rh-catalyzed direct synthesis of 2,2′-dihydroxybenzophenones and xanthones

An efficient rhodium-catalyzed direct synthesis of 2,2′-dihydroxybenzophenones and xanthones was developed from functionalized salicylaldehydes. This approach provides an easy access to various functionalized 2,2′-dihydroxybenzophenone and xanthone core s

2,2′-Dihydroxybenzophenones and their carbonyl N-analogues as inhibitor scaffolds for MDR-involved human glutathione transferase isoenzyme A1-1

The MDR-involved human GSTA1-1, an important isoenzyme overexpressed in several tumors leading to chemotherapeutic-resistant tumour cells, has been targeted by 2,2′-dihydroxybenzophenones and some of their carbonyl N-analogues, as its potential inhibitors. A structure-based library of the latter was built-up by a nucleophilic cleavage of suitably substituted xanthones to 2,2′-dihydroxy-benzophenones (5-9) and subsequent formation of their N-derivatives (oximes 11-13 and N-acyl hydrazones 14-16). Screening against hGSTA1-1 led to benzophenones 6 and 8, and hydrazones 14 and 16, having the highest inhibition potency (IC50 values in the range 0.18 ± 0.02 to 1.77 ± 0.10 μM). Enzyme inhibition kinetics, molecular modeling and docking studies showed that they interact primarily at the CDNB-binding catalytic site of the enzyme. In addition, the results from cytotoxicity studies with human colon adenocarcinoma cells showed low LC 50 values for benzophenone 6 and its N-acyl hydrazone analogue 14 (31.4 ± 0.4 μM and 87 ± 1.9 μM, respectively), in addition to the strong enzyme inhibition profile (IC50(6 ) = 1,77 ± 0.10 μM; IC50(14 ) = 0.33 ± 0.05 μM). These structures may serve as leads for the design of new potent mono- and bi-functional inhibitors and pro-drugs against human GTSs.

Pd/Cu-cocatalyzed aerobic oxidative carbonylative homocoupling of arylboronic acids and CO: A highly selective approach to diaryl ketones

A highly selective Pd/Cu-cocatalyzed aerobic oxidative carbonylative homocoupling of arylboronic acids has been developed. This method employs a simple catalytic system, readily available boronic acids as the substrates, molecular oxygen as the oxidant, and 1 atm of CO/O2, which makes this method practical for further applications.

Pd-catalyzed enantioselective C-H iodination: Asymmetric synthesis of chiral diarylmethylamines

An enantioselective C-H iodination reaction using a mono-N-benzoyl- protected amino acid has been developed for the synthesis of chiral diarylmethylamines. The reaction uses iodine as the sole oxidant and proceeds at ambient temperature and under air.

Broadening the catalyst and reaction scope of regio- and chemoselective C-H oxygenation: A convenient and scalable approach to 2-acylphenols by intriguing Rh(ii) and Ru(ii) catalysis

A unique Rh(ii) and Ru(ii) catalyzed C-H oxygenation of aryl ketones and other arenes has been developed for the facile synthesis of diverse functionalized phenols. The reaction demonstrates excellent reactivity, regio- and chemoselectivity, good functional group compatibility and high yields. The practicality of this method has been proved by gram-scale synthesis of a few different 2-acylphenols. Its utility has been well exemplified in further applications in heterocycle synthesis and direct modifications of drug Fenofibrate.

Synthesis of ortho-acylphenols through the palladium-catalyzed ketone-directed hydroxylation of arenes

ortho-Acylphenols are an important structural motif found in a diversity of bioactive molecules ranging from natural products to drugs (Figure 1). Moreover, they also serve as versatile building blocks for the synthesis of various pharmaceuticals, such as warfarin, as well as agrichemicals, flavors, and fragrances. Classic approaches to the synthesis of o-acylphenols generally involve a two-step process: acylation of phenols followed by Fries rearrangement of the resulting phenyl esters (Scheme 1a). On the other hand, direct C-acylation of phenols has also been known under more forcing conditions. Although effective, these approaches are often complicated by the formation of undesired p-substituted products when bulky acyl groups need to be introduced, as well as the limited variety of ketones that can be generated.

Ruthenium-catalyzed C-H bond oxygenations with weakly coordinating ketones

Ruthenium complexes enabled first C(sp2)-H bond oxygenations of aromatic ketones with excellent functional group tolerance, and broad scope as well as high chemoselectivity and site selectivity.